Sacramento or Reno
Every few years we remind ourselves why we don't ever ski Heavenly. It doesn't take long but there are some good runs like Gunbarrel/West Face in the morning before the bodies start stacking up. Kirkwood is quite a drive, especially in winter, as is Sierra at Tahoe in bad weather. My aversion to Heavenly may well be a North vs. South Shore thing though. No aversion to either of the other two South Shore resorts though
The drive from South Shore to Sacramento is a crap shoot because the storms come in from the Pacific every two or three days and dump on the western slopes while Reno is on the east of the Sierra in tha 'rain' shadow and gets considerably less snow. The obvious route from South Shore to Sacramento is Highway 50 which closes due to avalanche control while I-80 tends to stay open a lot more predictably but gets worse wind blown white-out conditions. It can take anywhere from 2 hours to 24 hours to get to Sacramento in winter. Reno is far more reliable.
The drive from South Shore to the North Shore resorts can be a challenge - frequently the western route (89) is closed due to avalanche danger at Emerald Bay although the eastern route is usually open until the 'accidents' close it down. I've never taken the boat but can see how it could work out OK, especially for Squaw.
Please be very scared when driving in poor (or marginal) conditions. Ignore the p*ss*d off locals and take your time.